{[4-(4-[2,2′]­Bipyridyl)­phenyl]­dimethylphosphine}dichloro(η⁵-penta­methyl­cycl­openta­dienyl)iridium(III)

The title compound, [Ir(Cp*)Cl₂(PC₁₈H₁₇N₂)], crystallizes with two mol­ecules in the asymmetric unit. The mol­ecules differ in geometry in the angles between the aromatic rings of the phosphine ligand.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.015 Å
• R factor = 0.040
• wR factor = 0.046
• Data-to-parameter ratio = 9.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
          Tmin and Tmax reported:      0.314     0.654
          Tmin' and Tmax expected:      0.400     0.654
          RR' =      0.785
          Please check that your absorption correction is appropriate.

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.78
         From the CIF: _reflns_number_total               8337
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         9165
         Completeness (_total/calc)             90.97%
          Alert C: < 95% complete

REFNR_01  Alert C Ratio of reflections to parameters is < 10 for a
          centrosymmetric structure
          sine(theta)/lambda                0.5897
          Proportion of unique data used    0.7009
          Ratio reflections to parameters   9.5318

THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5897

PLAT_213  Alert C Atom         has ADP max/min Ratio .............       3.10 C5


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 5 Alert Level C = Please check

---

S1. Comment

One form of C—H bond activation involves photochemically induced reductive elimination of molecular hydrogen from an Ir—Cp* dihydride complex (Janowicz & Bergman, 1983). The resulting electron-deficient species is able to oxidatively add hydrocarbons. Unfortunately, the photochemical reaction has a low quantum yield and also requires high energy photons.

Therefore, it would be advantageous to attach a chromophore to an Ir—Cp* dihydride. Efficient energy transfer from the chromophore would activate the Ir—Cp* center. The title compound, (I), possesses a bipyridine-functionalized linker intended to subsequently bind a rhenium chromophore. Transformation of the resulting dichloride into an Ir—Cp* dihydride may generate a complex with new and improved photochemical C—H bond activation.

This compound crystallized as orange parallelepipeds, following vapor diffusion of ether into a methylene chloride solution. The crystal structure confirmed that the molecule is an Ir(III) center coordinated in piano-stool fashion by an η⁵-Cp* ligand, two chlorides and a dimethyl aryl phosphine ligand. The aromatic arm of the phosphine is a p-phenyl-2,2'-bipyridine connected through the 5 position of the pyridine, giving the ligand an overall boomerang shape. There are two molecules of the complex in the asymmetric unit (Fig. 1). The molecules differ primarily in the conformation of the conjugated moiety. In one molecule, the three rings are close to coplanar; the proximal (C19–23, N1) and terminal (C24–28, N2) rings of the bipyridine form angles of 8.4° and 5.5° to the phenyl (C13–18) and 10.6° with each other. The three conjugated rings that comprise the moeity on the other molecule are twisted with respect to one another, with interplanar angles of 28.0° and 27.1° for the proximal (C47–51, N3) and terminal (C52–56, N4) rings to the phenyl ring (C41–46). The bipyridine in this second molecule is closer to planar than in the first, with an interplanar angle of 5.6°.

S2. Experimental

The title compound was prepared by stirring the phosphine ligand in a CH₂Cl₂ solution of IrCp*Cl₂ dimer at room temperature.

Computing details

Data collection: SMART (Bruker, 1995-1999); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare, 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1985, 1992); molecular graphics: please provide; software used to prepare material for publication: TEXSAN.

Figures

Fig. 1. Thermal ellipsoid plot (50% probability) of the asymmetric unit. The H atoms are removed for clarity.

(I)

Crystal data

[Ir(C10H15)(C18H17N2P)Cl2]	Z = 4
Mr = 690.67	F(000) = 1360.00
Triclinic, P1	Dx = 1.721 Mg m^−3
a = 13.592 (4) Å	Mo Kα radiation, λ = 0.7107 Å
b = 14.545 (4) Å	Cell parameters from 5533 reflections
c = 16.427 (4) Å	θ = 5.2–49.5°
α = 90.018 (4)°	µ = 5.30 mm^−1
β = 109.683 (4)°	T = 123 K
γ = 117.455 (4)°	Parallelepiped, orange
V = 2666 (1) Å^3	0.17 × 0.09 × 0.08 mm

Data collection

SMART CCD diffractometer	8337 independent reflections
Radiation source: X-ray tube	5843 reflections with I > 3.00σ(I)
Graphite monochromator	Rint = 0.038
ω–scan	θmax = 24.8°, θmin = 2.6°
Absorption correction: multi-scan (Blessing, 1995)	h = 0→15
Tmin = 0.314, Tmax = 0.654	k = −16→14
13236 measured reflections	l = −18→17

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	Weighting scheme based on measured s.u.'s Please provide expression for w
wR(F^2) = 0.046	(Δ/σ)max = 0.001
S = 1.23	Δρmax = 2.16 e Å^−3
5843 reflections	Δρmin = −2.33 e Å^−3
613 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ir1	0.62454 (3)	0.13409 (3)	0.75731 (2)	0.0167
Ir2	0.36902 (3)	0.36216 (3)	0.18745 (2)	0.0170
Cl1	0.7208 (2)	0.1084 (2)	0.9022 (1)	0.0226
Cl2	0.6824 (2)	0.0276 (2)	0.6931 (2)	0.0269
Cl3	0.2694 (2)	0.3808 (2)	0.2781 (2)	0.0260
Cl4	0.3013 (2)	0.4629 (2)	0.0892 (2)	0.0270
P1	0.8074 (2)	0.2767 (2)	0.7815 (2)	0.0199
P2	0.1906 (2)	0.2160 (2)	0.1076 (2)	0.0184
N1	0.8751 (7)	0.5878 (7)	0.3172 (5)	0.0276
N2	0.8207 (8)	0.3324 (7)	0.2364 (6)	0.0313
N3	0.0988 (8)	−0.0980 (7)	−0.4003 (5)	0.0260
N4	0.2193 (8)	0.1672 (7)	−0.4437 (5)	0.0264
C1	0.4291 (8)	0.0258 (7)	0.6776 (7)	0.0224
C2	0.4811 (9)	0.1222 (8)	0.6431 (6)	0.0215
C3	0.5182 (8)	0.2112 (8)	0.7097 (6)	0.0222
C4	0.5013 (8)	0.1697 (7)	0.7847 (6)	0.0187
C5	0.4427 (8)	0.0558 (7)	0.7631 (6)	0.0179
C6	0.375 (1)	−0.0825 (8)	0.6267 (7)	0.0349
C7	0.4792 (10)	0.1266 (10)	0.5523 (7)	0.0323
C8	0.5531 (10)	0.3189 (8)	0.6943 (7)	0.0309
C9	0.5189 (9)	0.2298 (8)	0.8675 (7)	0.0266
C10	0.4063 (9)	−0.0154 (8)	0.8262 (7)	0.0276
C11	0.8562 (9)	0.3798 (8)	0.8720 (6)	0.0270
C12	0.9301 (9)	0.2482 (9)	0.8115 (7)	0.0350
C13	0.8203 (8)	0.3430 (7)	0.6881 (6)	0.0201
C14	0.8428 (10)	0.4460 (8)	0.6899 (6)	0.0280
C15	0.8529 (10)	0.4927 (8)	0.6174 (7)	0.0290
C16	0.8438 (9)	0.4393 (8)	0.5425 (6)	0.0218
C17	0.8207 (9)	0.3369 (8)	0.5414 (6)	0.0268
C18	0.8080 (10)	0.2883 (8)	0.6126 (7)	0.0312
C19	0.8579 (8)	0.4918 (8)	0.4655 (6)	0.0208
C20	0.8914 (9)	0.5990 (9)	0.4687 (6)	0.0306
C21	0.8966 (9)	0.6411 (8)	0.3938 (7)	0.0284
C22	0.8473 (8)	0.4856 (8)	0.3160 (6)	0.0230
C23	0.8365 (9)	0.4348 (8)	0.3861 (7)	0.0226
C24	0.8284 (8)	0.4274 (8)	0.2324 (6)	0.0189
C25	0.8238 (9)	0.4711 (8)	0.1576 (7)	0.0297
C26	0.8101 (10)	0.4144 (9)	0.0824 (7)	0.0290
C27	0.8016 (9)	0.3185 (8)	0.0841 (7)	0.0265
C28	0.809 (1)	0.2808 (10)	0.1618 (7)	0.0385
C29	0.5600 (8)	0.4766 (8)	0.2145 (7)	0.0232
C30	0.5142 (9)	0.3812 (8)	0.1529 (6)	0.0252
C31	0.4859 (8)	0.2964 (8)	0.1977 (6)	0.0181
C32	0.5008 (9)	0.3346 (8)	0.2848 (6)	0.0216
C33	0.5525 (8)	0.4491 (8)	0.2952 (7)	0.0273
C34	0.6099 (9)	0.5871 (8)	0.1942 (7)	0.0289
C35	0.5115 (10)	0.3764 (9)	0.0593 (7)	0.0343
C36	0.4604 (9)	0.1885 (8)	0.1669 (7)	0.0277
C37	0.4907 (9)	0.2773 (8)	0.3585 (6)	0.0232
C38	0.5865 (10)	0.5210 (9)	0.3760 (7)	0.0332
C39	0.1477 (8)	0.1061 (8)	0.1658 (6)	0.0236
C40	0.0619 (8)	0.2367 (8)	0.0725 (6)	0.0236
C41	0.1828 (8)	0.1589 (7)	0.0056 (6)	0.0179
C42	0.1720 (8)	0.2084 (7)	−0.0677 (6)	0.0216
C43	0.1597 (9)	0.1612 (8)	−0.1478 (6)	0.0226
C44	0.1621 (8)	0.0675 (8)	−0.1544 (6)	0.0147
C45	0.1809 (8)	0.0215 (7)	−0.0795 (6)	0.0187
C46	0.1887 (8)	0.0661 (7)	−0.0013 (6)	0.0180
C47	0.1404 (8)	0.0119 (8)	−0.2402 (6)	0.0190
C48	0.1698 (8)	0.0647 (8)	−0.3058 (6)	0.0176
C49	0.1448 (9)	0.0080 (9)	−0.3861 (6)	0.0250
C50	0.0714 (9)	−0.1475 (8)	−0.3370 (7)	0.0301
C51	0.0877 (9)	−0.0982 (8)	−0.2576 (6)	0.0226
C52	0.1694 (9)	0.0611 (8)	−0.4590 (6)	0.0229
C53	0.2358 (10)	0.2142 (9)	−0.5120 (7)	0.0349
C54	0.2069 (9)	0.1611 (9)	−0.5949 (6)	0.0264
C55	0.1563 (9)	0.0531 (8)	−0.6083 (6)	0.0253
C56	0.1361 (8)	0.0018 (8)	−0.5401 (6)	0.0239
H1	0.3092	−0.0937	0.5743	0.0419*
H2	0.3462	−0.1332	0.6613	0.0419*
H3	0.4328	−0.0892	0.6118	0.0419*
H4	0.5194	0.0918	0.5416	0.0388*
H5	0.5183	0.1978	0.5460	0.0388*
H6	0.3985	0.0921	0.5113	0.0388*
H7	0.6202	0.3444	0.6774	0.0370*
H8	0.5737	0.3632	0.7465	0.0370*
H9	0.4881	0.3194	0.6484	0.0370*
H10	0.5993	0.2851	0.8934	0.0319*
H11	0.5016	0.1834	0.9077	0.0319*
H12	0.4662	0.2584	0.8537	0.0319*
H13	0.3687	−0.0868	0.7984	0.0331*
H14	0.3521	−0.0041	0.8434	0.0331*
H15	0.4754	−0.0001	0.8768	0.0331*
H16	0.9293	0.4388	0.8757	0.0324*
H17	0.8679	0.3537	0.9255	0.0324*
H18	0.7968	0.4002	0.8620	0.0324*
H19	0.9127	0.1946	0.7673	0.0420*
H20	0.9402	0.2248	0.8661	0.0420*
H21	1.0016	0.3102	0.8165	0.0420*
H22	0.8507	0.4845	0.7406	0.0336*
H23	0.8664	0.5630	0.6189	0.0348*
H24	0.8131	0.2984	0.4908	0.0321*
H25	0.7908	0.2170	0.6099	0.0374*
H26	0.9102	0.6420	0.5213	0.0367*
H27	0.9170	0.7131	0.3966	0.0341*
H28	0.8149	0.3622	0.3810	0.0272*
H29	0.8297	0.5387	0.1573	0.0356*
H30	0.8071	0.4434	0.0303	0.0347*
H31	0.7908	0.2777	0.0335	0.0318*
H32	0.8049	0.2140	0.1631	0.0462*
H33	0.6914	0.6287	0.2328	0.0347*
H34	0.5649	0.6181	0.2021	0.0347*
H35	0.6048	0.5838	0.1350	0.0347*
H36	0.5342	0.4445	0.0442	0.0411*
H37	0.4326	0.3280	0.0194	0.0411*
H38	0.5656	0.3542	0.0556	0.0411*
H39	0.3927	0.1576	0.1128	0.0332*
H40	0.4439	0.1461	0.2097	0.0332*
H41	0.5279	0.1924	0.1584	0.0332*
H42	0.4554	0.2040	0.3377	0.0279*
H43	0.4417	0.2891	0.3822	0.0279*
H44	0.5680	0.3020	0.4029	0.0279*
H45	0.6693	0.5721	0.3956	0.0399*
H46	0.5727	0.4813	0.4208	0.0399*
H47	0.5400	0.5555	0.3636	0.0399*
H48	0.0772	0.0464	0.1268	0.0283*
H49	0.1334	0.1252	0.2141	0.0283*
H50	0.2109	0.0894	0.1867	0.0283*
H51	0.0693	0.2834	0.0317	0.0284*
H52	0.0582	0.2664	0.1221	0.0284*
H53	−0.0091	0.1711	0.0452	0.0284*
H54	0.1730	0.2739	−0.0633	0.0259*
H55	0.1498	0.1940	−0.1978	0.0271*
H56	0.1885	−0.0399	−0.0823	0.0224*
H57	0.1984	0.0330	0.0483	0.0216*
H58	0.2069	0.1395	−0.2966	0.0211*
H59	0.0378	−0.2220	−0.3468	0.0362*
H60	0.0637	−0.1383	−0.2155	0.0271*
H61	0.2690	0.2885	−0.5036	0.0419*
H62	0.2221	0.1986	−0.6404	0.0317*
H63	0.1358	0.0145	−0.6636	0.0304*
H64	0.0996	−0.0728	−0.5482	0.0287*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir(1)	0.0192 (2)	0.0164 (2)	0.0161 (2)	0.0117 (2)	0.0047 (2)	0.0028 (2)
Ir(2)	0.0193 (2)	0.0148 (2)	0.0170 (2)	0.0102 (2)	0.0046 (2)	0.0023 (2)
Cl(1)	0.028 (1)	0.022 (1)	0.020 (1)	0.015 (1)	0.005 (1)	0.007 (1)
Cl(2)	0.033 (1)	0.026 (1)	0.030 (1)	0.021 (1)	0.013 (1)	0.004 (1)
Cl(3)	0.031 (1)	0.028 (1)	0.022 (1)	0.017 (1)	0.008 (1)	0.000 (1)
Cl(4)	0.030 (1)	0.021 (1)	0.028 (1)	0.016 (1)	0.007 (1)	0.010 (1)
P(1)	0.022 (1)	0.024 (1)	0.016 (1)	0.014 (1)	0.006 (1)	0.005 (1)
P(2)	0.020 (1)	0.023 (1)	0.014 (1)	0.014 (1)	0.003 (1)	0.004 (1)
N(1)	0.024 (5)	0.025 (5)	0.027 (5)	0.008 (4)	0.009 (4)	0.004 (4)
N(2)	0.045 (6)	0.021 (5)	0.037 (5)	0.021 (5)	0.024 (5)	0.011 (4)
N(3)	0.035 (5)	0.032 (5)	0.018 (4)	0.018 (5)	0.013 (4)	0.004 (4)
N(4)	0.037 (5)	0.030 (5)	0.012 (4)	0.014 (4)	0.008 (4)	0.003 (4)
C(1)	0.015 (5)	0.015 (5)	0.033 (6)	0.008 (4)	0.006 (4)	0.003 (5)
C(2)	0.030 (6)	0.034 (6)	0.014 (5)	0.022 (5)	0.007 (4)	0.003 (5)
C(3)	0.018 (5)	0.023 (6)	0.026 (5)	0.016 (5)	0.000 (4)	0.003 (5)
C(4)	0.020 (5)	0.010 (5)	0.027 (5)	0.012 (4)	0.007 (4)	0.004 (4)
C(5)	0.011 (5)	0.018 (5)	0.028 (6)	0.012 (4)	0.001 (4)	0.001 (5)
C(6)	0.049 (7)	0.024 (6)	0.028 (6)	0.024 (6)	0.003 (5)	−0.005 (5)
C(7)	0.032 (6)	0.053 (8)	0.024 (6)	0.028 (6)	0.005 (5)	0.004 (5)
C(8)	0.035 (6)	0.027 (6)	0.032 (6)	0.020 (5)	0.005 (5)	0.001 (5)
C(9)	0.030 (6)	0.027 (6)	0.028 (6)	0.020 (5)	0.012 (5)	0.006 (5)
C(10)	0.032 (6)	0.021 (6)	0.039 (6)	0.008 (5)	0.025 (5)	0.013 (5)
C(11)	0.032 (6)	0.021 (6)	0.022 (5)	0.011 (5)	0.006 (5)	0.003 (5)
C(12)	0.029 (6)	0.036 (7)	0.043 (7)	0.023 (6)	0.013 (5)	0.015 (5)
C(13)	0.019 (5)	0.019 (5)	0.018 (5)	0.011 (4)	0.005 (4)	0.003 (4)
C(14)	0.040 (6)	0.021 (6)	0.024 (5)	0.017 (5)	0.017 (5)	0.011 (5)
C(15)	0.039 (7)	0.022 (6)	0.032 (6)	0.017 (5)	0.019 (5)	0.012 (5)
C(16)	0.020 (5)	0.030 (6)	0.025 (6)	0.018 (5)	0.009 (4)	0.005 (5)
C(17)	0.037 (6)	0.025 (6)	0.020 (5)	0.012 (5)	0.013 (5)	0.003 (5)
C(18)	0.042 (7)	0.021 (6)	0.032 (6)	0.015 (5)	0.015 (5)	0.004 (5)
C(19)	0.011 (5)	0.031 (6)	0.016 (5)	0.006 (5)	0.003 (4)	0.005 (5)
C(20)	0.030 (6)	0.035 (7)	0.019 (5)	0.011 (5)	0.011 (5)	0.006 (5)
C(21)	0.034 (6)	0.012 (5)	0.027 (6)	0.000 (5)	0.010 (5)	0.005 (5)
C(22)	0.013 (5)	0.032 (7)	0.019 (5)	0.005 (5)	0.007 (4)	0.003 (5)
C(23)	0.023 (6)	0.022 (6)	0.031 (6)	0.014 (5)	0.014 (5)	0.014 (5)
C(24)	0.016 (5)	0.016 (5)	0.018 (5)	0.005 (4)	0.003 (4)	0.007 (4)
C(25)	0.034 (6)	0.030 (6)	0.022 (6)	0.018 (5)	0.005 (5)	0.016 (5)
C(26)	0.035 (6)	0.034 (7)	0.022 (6)	0.018 (6)	0.012 (5)	0.011 (5)
C(27)	0.031 (6)	0.024 (6)	0.023 (6)	0.006 (5)	0.013 (5)	0.002 (5)
C(28)	0.057 (8)	0.039 (7)	0.030 (6)	0.020 (6)	0.026 (6)	0.009 (6)
C(29)	0.017 (5)	0.014 (5)	0.032 (6)	0.008 (4)	0.003 (4)	0.004 (5)
C(30)	0.027 (6)	0.023 (6)	0.025 (6)	0.015 (5)	0.008 (5)	0.000 (5)
C(31)	0.010 (5)	0.019 (5)	0.021 (5)	0.006 (4)	0.002 (4)	−0.002 (4)
C(32)	0.021 (5)	0.025 (6)	0.019 (5)	0.013 (5)	−0.001 (4)	−0.002 (5)
C(33)	0.016 (5)	0.024 (6)	0.029 (6)	0.011 (5)	−0.005 (4)	−0.002 (5)
C(34)	0.025 (6)	0.024 (6)	0.037 (6)	0.008 (5)	0.011 (5)	0.013 (5)
C(35)	0.037 (7)	0.030 (7)	0.035 (6)	0.012 (6)	0.018 (5)	0.000 (5)
C(36)	0.022 (5)	0.026 (6)	0.038 (6)	0.019 (5)	0.005 (5)	0.004 (5)
C(37)	0.024 (6)	0.024 (6)	0.016 (5)	0.008 (5)	0.003 (4)	0.002 (4)
C(38)	0.033 (6)	0.028 (6)	0.028 (6)	0.015 (5)	−0.005 (5)	−0.005 (5)
C(39)	0.023 (5)	0.029 (6)	0.010 (5)	0.009 (5)	0.007 (4)	0.006 (4)
C(40)	0.021 (5)	0.032 (6)	0.014 (5)	0.014 (5)	0.003 (4)	−0.002 (4)
C(41)	0.012 (5)	0.019 (5)	0.020 (5)	0.007 (4)	0.004 (4)	−0.001 (4)
C(42)	0.022 (5)	0.010 (5)	0.028 (6)	0.004 (4)	0.011 (5)	0.006 (4)
C(43)	0.023 (5)	0.027 (6)	0.016 (5)	0.012 (5)	0.007 (4)	0.004 (4)
C(44)	0.013 (5)	0.023 (6)	0.012 (5)	0.008 (4)	0.007 (4)	−0.002 (4)
C(45)	0.023 (5)	0.017 (5)	0.020 (5)	0.014 (5)	0.010 (4)	0.007 (4)
C(46)	0.018 (5)	0.018 (5)	0.018 (5)	0.010 (4)	0.005 (4)	0.005 (4)
C(47)	0.015 (5)	0.037 (6)	0.010 (5)	0.015 (5)	0.005 (4)	0.001 (4)
C(48)	0.021 (5)	0.017 (5)	0.017 (5)	0.011 (5)	0.002 (4)	0.004 (4)
C(49)	0.024 (6)	0.042 (7)	0.011 (5)	0.020 (5)	0.003 (4)	0.008 (5)
C(50)	0.033 (6)	0.021 (6)	0.027 (6)	0.008 (5)	0.006 (5)	0.001 (5)
C(51)	0.026 (6)	0.029 (6)	0.012 (5)	0.016 (5)	0.002 (4)	0.002 (4)
C(52)	0.020 (5)	0.024 (6)	0.023 (5)	0.012 (5)	0.006 (4)	0.005 (5)
C(53)	0.036 (7)	0.037 (7)	0.025 (6)	0.017 (6)	0.004 (5)	0.007 (5)
C(54)	0.033 (6)	0.042 (7)	0.018 (5)	0.018 (6)	0.010 (5)	0.006 (5)
C(55)	0.031 (6)	0.033 (7)	0.017 (5)	0.022 (5)	0.006 (5)	0.006 (5)
C(56)	0.022 (5)	0.031 (6)	0.019 (5)	0.019 (5)	0.004 (4)	0.004 (5)

Geometric parameters (Å, º)

IR1—CL1	2.423 (2)	C49—C52	1.47 (1)
IR1—CL2	2.410 (2)	C50—C51	1.39 (1)
IR1—P1	2.285 (3)	C52—C56	1.40 (1)
IR1—C1	2.247 (9)	C53—C54	1.40 (1)
IR1—C2	2.139 (9)	C54—C55	1.38 (1)
IR1—C3	2.167 (9)	C55—C56	1.38 (1)
IR1—C4	2.141 (9)	C6—H1	0.9500
IR1—C5	2.231 (9)	C6—H2	0.9500
IR2—CL3	2.412 (2)	C6—H3	0.9500
IR2—CL4	2.418 (2)	C7—H4	0.9500
IR2—P2	2.285 (2)	C7—H5	0.9500
IR2—C29	2.224 (9)	C7—H6	0.9500
IR2—C30	2.131 (10)	C8—H7	0.9500
IR2—C31	2.165 (9)	C8—H8	0.9500
IR2—C32	2.158 (9)	C8—H9	0.9500
IR2—C33	2.251 (9)	C9—H10	0.9500
P1—C11	1.821 (10)	C9—H11	0.9500
P1—C12	1.81 (1)	C9—H12	0.9500
P1—C13	1.827 (10)	C10—H13	0.9500
P2—C39	1.824 (10)	C10—H14	0.9500
P2—C40	1.813 (10)	C10—H15	0.9500
P2—C41	1.817 (9)	C11—H16	0.9500
N1—C21	1.35 (1)	C11—H17	0.9500
N1—C22	1.35 (1)	C11—H18	0.9500
N2—C24	1.34 (1)	C12—H19	0.9500
N2—C28	1.36 (1)	C12—H20	0.9500
N3—C49	1.36 (1)	C12—H21	0.9500
N3—C50	1.32 (1)	C14—H22	0.9500
N4—C52	1.35 (1)	C15—H23	0.9500
N4—C53	1.34 (1)	C17—H24	0.9500
C1—C2	1.46 (1)	C18—H25	0.9500
C1—C5	1.40 (1)	C20—H26	0.9500
C1—C6	1.49 (1)	C21—H27	0.9500
C2—C3	1.47 (1)	C23—H28	0.9500
C2—C7	1.49 (1)	C25—H29	0.9500
C3—C4	1.41 (1)	C26—H30	0.9500
C3—C8	1.46 (1)	C27—H31	0.9500
C4—C5	1.45 (1)	C28—H32	0.9500
C4—C9	1.50 (1)	C34—H33	0.9500
C5—C10	1.50 (1)	C34—H34	0.9500
C13—C14	1.38 (1)	C34—H35	0.9500
C13—C18	1.39 (1)	C35—H36	0.9500
C14—C15	1.39 (1)	C35—H37	0.9500
C15—C16	1.39 (1)	C35—H38	0.9500
C16—C17	1.37 (1)	C36—H39	0.9500
C16—C19	1.50 (1)	C36—H40	0.9500
C17—C18	1.39 (1)	C36—H41	0.9500
C19—C20	1.40 (1)	C37—H42	0.9500
C19—C23	1.41 (1)	C37—H43	0.9500
C20—C21	1.38 (1)	C37—H44	0.9500
C22—C23	1.38 (1)	C38—H45	0.9500
C22—C24	1.49 (1)	C38—H46	0.9500
C24—C25	1.38 (1)	C38—H47	0.9500
C25—C26	1.39 (1)	C39—H48	0.9500
C26—C27	1.35 (1)	C39—H49	0.9500
C27—C28	1.38 (1)	C39—H50	0.9500
C29—C30	1.45 (1)	C40—H51	0.9500
C29—C33	1.41 (1)	C40—H52	0.9500
C29—C34	1.52 (1)	C40—H53	0.9500
C30—C31	1.40 (1)	C42—H54	0.9500
C30—C35	1.53 (1)	C43—H55	0.9500
C31—C32	1.45 (1)	C45—H56	0.9500
C31—C36	1.49 (1)	C46—H57	0.9500
C32—C33	1.46 (1)	C48—H58	0.9500
C32—C37	1.48 (1)	C50—H59	0.9500
C33—C38	1.49 (1)	C51—H60	0.9500
C41—C42	1.40 (1)	C53—H61	0.9500
C47—C48	1.39 (1)	C54—H62	0.9500
C47—C51	1.40 (1)	C55—H63	0.9500
C48—C49	1.40 (1)	C56—H64	0.9500
CL1—IR1—CL2	89.98 (8)	C3—C8—H7	109.4738
CL1—IR1—P1	85.58 (8)	C3—C8—H8	109.4734
CL2—IR1—P1	88.71 (9)	C3—C8—H9	109.4721
CL3—IR2—CL4	90.05 (9)	H7—C8—H8	109.4698
CL3—IR2—P2	86.38 (9)	H7—C8—H9	109.4687
CL4—IR2—P2	87.45 (8)	H8—C8—H9	109.4695
IR1—P1—C11	113.5 (3)	C4—C9—H10	109.4745
IR1—P1—C12	114.6 (4)	C4—C9—H11	109.4719
IR1—P1—C13	115.8 (3)	C4—C9—H12	109.4735
C11—P1—C12	103.2 (5)	H10—C9—H11	109.4697
C11—P1—C13	105.4 (4)	H10—C9—H12	109.4713
C12—P1—C13	102.9 (5)	H11—C9—H12	109.4665
IR2—P2—C39	114.4 (3)	C5—C10—H13	109.4669
IR2—P2—C40	114.8 (3)	C5—C10—H14	109.4694
IR2—P2—C41	115.3 (3)	C5—C10—H15	109.4664
C39—P2—C40	103.6 (5)	H13—C10—H14	109.4761
C39—P2—C41	104.0 (4)	H13—C10—H15	109.4736
C40—P2—C41	103.3 (4)	H14—C10—H15	109.4749
C21—N1—C22	115.7 (9)	P1—C11—H16	109.4705
C24—N2—C28	115.9 (9)	P1—C11—H17	109.4704
C49—N3—C50	117.2 (8)	P1—C11—H18	109.4717
C52—N4—C53	115.8 (9)	H16—C11—H17	109.4709
C2—C1—C5	107.5 (8)	H16—C11—H18	109.4712
C2—C1—C6	123.4 (9)	H17—C11—H18	109.4726
C5—C1—C6	129.1 (9)	P1—C12—H19	109.4729
C1—C2—C3	107.3 (8)	P1—C12—H20	109.4716
C1—C2—C7	125.5 (9)	P1—C12—H21	109.4735
C3—C2—C7	126.7 (9)	H19—C12—H20	109.4689
C2—C3—C4	106.8 (8)	H19—C12—H21	109.4715
C2—C3—C8	124.2 (9)	H20—C12—H21	109.4690
C4—C3—C8	128.6 (9)	C13—C14—H22	120.0631
C3—C4—C5	108.7 (8)	C15—C14—H22	120.0657
C3—C4—C9	126.2 (9)	C14—C15—H23	119.1267
C5—C4—C9	124.2 (9)	C16—C15—H23	119.1317
C1—C5—C4	109.3 (9)	C16—C17—H24	119.3656
C1—C5—C10	127.1 (9)	C18—C17—H24	119.3661
C4—C5—C10	123.5 (8)	C13—C18—H25	119.6818
P1—C13—C14	122.3 (7)	C17—C18—H25	119.6828
P1—C13—C18	118.9 (8)	C19—C20—H26	120.7834
C14—C13—C18	118.8 (9)	C21—C20—H26	120.7803
C13—C14—C15	119.9 (9)	N1—C21—H27	117.3910
C14—C15—C16	121.7 (10)	C20—C21—H27	117.3979
C15—C16—C17	117.7 (9)	C19—C23—H28	120.4649
C15—C16—C19	121.1 (10)	C22—C23—H28	120.4662
C17—C16—C19	121.2 (9)	C24—C25—H29	120.3488
C16—C17—C18	121.3 (9)	C26—C25—H29	120.3575
C13—C18—C17	120.6 (10)	C25—C26—H30	120.3415
C16—C19—C20	121.5 (9)	C27—C26—H30	120.3395
C16—C19—C23	121.1 (9)	C26—C27—H31	120.9388
C20—C19—C23	117.4 (9)	C28—C27—H31	120.9394
C19—C20—C21	118.4 (9)	N2—C28—H32	117.6701
N1—C21—C20	125.2 (10)	C27—C28—H32	117.6650
N1—C22—C23	124.1 (9)	C29—C34—H33	109.4729
N1—C22—C24	115.9 (9)	C29—C34—H34	109.4719
C23—C22—C24	120.0 (10)	C29—C34—H35	109.4726
C19—C23—C22	119.1 (10)	H33—C34—H34	109.4706
N2—C24—C22	115.4 (9)	H33—C34—H35	109.4700
N2—C24—C25	122.7 (10)	H34—C34—H35	109.4693
C22—C24—C25	121.9 (10)	C30—C35—H36	109.4751
C24—C25—C26	119 (1)	C30—C35—H37	109.4767
C25—C26—C27	119.3 (10)	C30—C35—H38	109.4779
C26—C27—C28	118 (1)	H36—C35—H37	109.4646
N2—C28—C27	124 (1)	H36—C35—H38	109.4674
C30—C29—C33	108.8 (9)	H37—C35—H38	109.4657
C30—C29—C34	124.8 (9)	C31—C36—H39	109.4707
C33—C29—C34	126.4 (9)	C31—C36—H40	109.4709
C29—C30—C31	108.1 (8)	C31—C36—H41	109.4706
C29—C30—C35	125.6 (9)	H39—C36—H40	109.4715
C31—C30—C35	125.8 (9)	H39—C36—H41	109.4727
C30—C31—C32	108.3 (8)	H40—C36—H41	109.4709
C30—C31—C36	126.7 (9)	C32—C37—H42	109.4691
C32—C31—C36	124.5 (9)	C32—C37—H43	109.4697
C31—C32—C33	107.1 (9)	C32—C37—H44	109.4669
C31—C32—C37	128.8 (9)	H42—C37—H43	109.4750
C33—C32—C37	123.1 (9)	H42—C37—H44	109.4723
C29—C33—C32	107.2 (9)	H43—C37—H44	109.4744
C29—C33—C38	127.5 (10)	C33—C38—H45	109.4708
C32—C33—C38	125.3 (10)	C33—C38—H46	109.4743
P2—C41—C42	120.4 (7)	C33—C38—H47	109.4747
P2—C41—C46	121.2 (7)	H45—C38—H46	109.4671
C42—C41—C46	118.4 (8)	H45—C38—H47	109.4680
C41—C42—C43	120.3 (9)	H46—C38—H47	109.4724
C42—C43—C44	120.3 (9)	P2—C39—H48	109.4700
C43—C44—C45	119.4 (8)	P2—C39—H49	109.4681
C43—C44—C47	121.4 (9)	P2—C39—H50	109.4701
C45—C44—C47	119.2 (9)	H48—C39—H49	109.4718
C44—C45—C46	120.1 (9)	H48—C39—H50	109.4748
C41—C46—C45	121.2 (9)	H49—C39—H50	109.4726
C44—C47—C48	122.7 (9)	P2—C40—H51	109.4691
C44—C47—C51	120.3 (9)	P2—C40—H52	109.4697
C48—C47—C51	116.9 (8)	P2—C40—H53	109.4694
C47—C48—C49	120.2 (9)	H51—C40—H52	109.4732
N3—C49—C48	122.0 (9)	H51—C40—H53	109.4724
N3—C49—C52	116.4 (9)	H52—C40—H53	109.4734
C48—C49—C52	121.6 (10)	C41—C42—H54	119.8409
N3—C50—C51	124.4 (10)	C43—C42—H54	119.8460
C47—C51—C50	119.1 (9)	C42—C43—H55	119.8286
N4—C52—C49	116.4 (9)	C44—C43—H55	119.8251
N4—C52—C56	123.3 (9)	C44—C45—H56	119.9704
C49—C52—C56	120.2 (10)	C46—C45—H56	119.9662
N4—C53—C54	124 (1)	C41—C46—H57	119.3860
C53—C54—C55	118.2 (10)	C45—C46—H57	119.3884
C54—C55—C56	118.8 (9)	C47—C48—H58	119.9178
C52—C56—C55	119.2 (10)	C49—C48—H58	119.9194
C1—C6—H1	109.4727	N3—C50—H59	117.7825
C1—C6—H2	109.4737	C51—C50—H59	117.7836
C1—C6—H3	109.4732	C47—C51—H60	120.4467
H1—C6—H2	109.4684	C50—C51—H60	120.4497
H1—C6—H3	109.4696	N4—C53—H61	117.6937
H2—C6—H3	109.4697	C54—C53—H61	117.6895
C2—C7—H4	109.4716	C53—C54—H62	120.8919
C2—C7—H5	109.4742	C55—C54—H62	120.8927
C2—C7—H6	109.4725	C54—C55—H63	120.5786
H4—C7—H5	109.4683	C56—C55—H63	120.5791
H4—C7—H6	109.4684	C52—C56—H64	120.3925
H5—C7—H6	109.4724	C55—C56—H64	120.3937